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TWI455919B - Method for preparing 3-trifluoromethylchalcone (CHALCONE) - Google Patents

Method for preparing 3-trifluoromethylchalcone (CHALCONE) Download PDF

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Publication number
TWI455919B
TWI455919B TW098109424A TW98109424A TWI455919B TW I455919 B TWI455919 B TW I455919B TW 098109424 A TW098109424 A TW 098109424A TW 98109424 A TW98109424 A TW 98109424A TW I455919 B TWI455919 B TW I455919B
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TW
Taiwan
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group
alkyl
formula
independently
compound
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TW098109424A
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Chinese (zh)
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TW200948770A (en
Inventor
Gary David Annis
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Du Pont
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
    • C07C209/74—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton by halogenation, hydrohalogenation, dehalogenation, or dehydrohalogenation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
    • C—CHEMISTRY; METALLURGY
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/14—Preparation of carboxylic acid amides by formation of carboxamide groups together with reactions not involving the carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/84—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
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    • C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
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    • C07C25/13—Monocyclic aromatic halogenated hydrocarbons containing fluorine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/455—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation with carboxylic acids or their derivatives
    • C—CHEMISTRY; METALLURGY
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    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
    • C07C49/813—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen polycyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/32—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups
    • C07C65/38—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups having unsaturation outside the aromatic rings
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
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    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D—HETEROCYCLIC COMPOUNDS
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    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/16—Halogen atoms or nitro radicals
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    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

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  • Wood Science & Technology (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Plural Heterocyclic Compounds (AREA)

Claims (15)

一種用於製備式1化合物之方法 其中Z係視情況經取代之苯基；且Q係苯基或1-萘基，其各自視情況經取代；該方法包括自包含下述之混合物中蒸餾出水：式2化合物； 式3化合物； 鹼，該鹼包含至少一種選自由下述組成之群的化合物：式4鹼土金屬氫氧化物M(OH)24其中M係Ca、Sr或Ba，式4a鹼金屬碳酸鹽(M1)2CO34a其中M1係Li、Na或K， 1,5-二氮雜二環[4.3.0]壬-5-烯及1,8-二氮雜二環[5.4.0]十一碳-7-烯；及能夠與水形成低沸點共沸物之非質子性溶劑。 Method for preparing compound of formula 1 Wherein Z is optionally substituted phenyl; and Q is phenyl or 1-naphthyl, each of which is optionally substituted; the method comprises distilling water from a mixture comprising: a compound of formula 2; a compound of formula 3; a base comprising at least one compound selected from the group consisting of: an alkaline earth metal hydroxide M(OH) 24 of the formula 4 wherein M is Ca, Sr or Ba, and an alkali metal carbonate of the formula 4a (M1) 2CO34a wherein M1 Li, Na or K, 1,5-diazabicyclo[4.3.0]non-5-ene and 1,8-diazabicyclo[5.4.0]undec-7-ene; and capable of forming a low boiling point with water An aprotic solvent for the boil. 如請求項1之方法，其中該鹼包含式4鹼土金屬氫氧化物且該混合物進一步包含極性非質子性溶劑。 The method of claim 1, wherein the base comprises an alkaline earth metal hydroxide of formula 4 and the mixture further comprises a polar aprotic solvent. 如請求項2之方法，其中M係Ca。 The method of claim 2, wherein M is Ca. 如請求項2之方法，其中該極性非質子性溶劑包含N,N-二甲基甲醯胺。 The method of claim 2, wherein the polar aprotic solvent comprises N,N-dimethylformamide. 如請求項2之方法，其中能夠與水形成低沸點共沸物之該非質子性溶劑包含第三丁基甲基醚。 The method of claim 2, wherein the aprotic solvent capable of forming a low boiling azeotrope with water comprises a third butyl methyl ether. 如請求項1之方法，其中該鹼包含式4a鹼金屬碳酸鹽。 The method of claim 1, wherein the base comprises an alkali metal carbonate of the formula 4a. 如請求項6之方法，其中M1係K。 The method of claim 6, wherein M1 is K. 如請求項1之方法，其中該鹼包含1,5-二氮雜二環[4.3.0]壬-5-烯、1,8-二氮雜二環[5.4.0]十一碳-7-烯、或其混合物。 The method of claim 1, wherein the base comprises 1,5-diazabicyclo[4.3.0]non-5-ene, 1,8-diazabicyclo[5.4.0]undec-7 - alkene, or a mixture thereof. 如請求項6、7或8中任一項之方法，其中能夠與水形成低沸點共沸物之該非質子性溶劑包含乙腈。 The method of any one of claims 6, 7 or 8, wherein the aprotic solvent capable of forming a low boiling azeotrope with water comprises acetonitrile. 如請求項1之方法，其中：Z係視情況經至多5個獨立選自R2之取代基取代之苯基；Q係苯基或1-萘基，其各自視情況經至多4個獨立選自R3之取代基取代；各R2獨立地為鹵素、C1-C6烷基、C1-C6鹵代烷基、C1-C6烷氧基、C1-C6鹵代烷氧基、C1-C6烷硫基、C1-C6 鹵代烷硫基、C1-C6烷基胺基、C2-C6二烷基胺基、-CN或-NO2；各R3獨立地為鹵素、C1-C6烷基、C1-C6鹵代烷基、C2-C6烯基、C2-C6鹵代烯基、C2-C6炔基、C3-C6鹵代炔基、C3-C6環烷基、C3-C6鹵代環烷基、C1-C6烷氧基、C1-C6鹵代烷氧基、C1-C6烷硫基、C2-C7烷基羰基、C2-C7鹵代烷基羰基、C1-C6鹵代烷硫基、C1-C6烷基亞磺醯基、C1-C6鹵代烷基亞磺醯基、C1-C6烷基磺醯基、C1-C6鹵代烷基磺醯基、-N(R4)R5、-C(=W)N(R4)R5、-C(=W)OR5、-CN、-OR11或-NO2；或苯環或5-員或6-員飽和或不飽和雜環，各環視情況經一個或多個獨立地選自下述之取代基取代：鹵素、C1-C6烷基、C1-C6鹵代烷基、C3-C6環烷基、C3-C6鹵代環烷基、C1-C6烷氧基、C1-C6鹵代烷氧基、C1-C6烷硫基、C1-C6鹵代烷硫基、C1-C6烷基亞磺醯基、C1-C6鹵代烷基亞磺醯基、C1-C6烷基磺醯基、C1-C6鹵代烷基磺醯基、-CN、-NO2、-N(R4)R5、-C(=W)N(R4)R5、-C(=O)OR5及R7；各R4獨立地為H、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6環烷基、C4-C7烷基環烷基、C4-C7環烷基烷基、C2-C7烷基羰基或C2-C7烷氧基羰基；各R5獨立地為H；或C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6環烷基、C4-C7烷基環烷基或C4-C7環烷基烷基，各自視情況經一個或多個獨立地選自R6之取代基取代； 各R6獨立地為鹵素、C1-C6烷基、C1-C6烷氧基、C1-C6烷硫基、C1-C6烷基亞磺醯基、C1-C6烷基磺醯基、C1-C6烷基胺基、C2-C8二烷基胺基、C3-C6環烷基胺基、C2-C7烷基羰基、C2-C7烷氧基羰基、C2-C7烷基胺基羰基、C3-C9二烷基胺基羰基、C2-C7鹵代烷基羰基、C2-C7鹵代烷氧基羰基、C2-C7鹵代烷基胺基羰基、C3-C9鹵代二烷基胺基羰基、-OH、-NH2、-CN或-NO2；或Q1；各R7獨立地為苯環或吡啶基環，各環視情況經一個或多個獨立地選自R8之取代基取代；各R8獨立地為鹵素、C1-C6烷基、C1-C6鹵代烷基、C1-C6烷氧基、C1-C6鹵代烷氧基、C1-C6烷硫基、C1-C6鹵代烷硫基、C1-C6烷基亞磺醯基、C1-C6鹵代烷基亞磺醯基、C1-C6烷基磺醯基、C1-C6鹵代烷基磺醯基、C1-C6烷基胺基、C2-C6二烷基胺基、C2-C4烷基羰基、C2-C4烷氧基羰基、C2-C7烷基胺基羰基、C3-C7二烷基胺基羰基、-OH、-NH2、-C(=O)OH、-CN或-NO2；各Q1獨立地為苯環或5-員或6-員飽和或不飽和雜環，各環視情況經一個或多個獨立地選自下述之取代基取代：鹵素、C1-C6烷基、C1-C6鹵代烷基、C3-C6環烷基、C3-C6鹵代環烷基、C1-C6烷氧基、C1-C6鹵代烷氧基、C1-C6烷硫基、C1-C6鹵代烷硫基、C1-C6烷基亞磺醯基、C1-C6鹵代烷基亞磺醯基、C1-C6烷基磺醯基、C1-C6鹵代烷基磺醯基、C1-C6烷基胺基、C2-C6二 烷基胺基、-CN、-NO2、-C(=W)N(R9)R10及-C(=O)OR10；各R9獨立地為H、C1-C6烷基、C1-C6鹵代烷基、C2-C6烯基、C2-C6炔基、C3-C6環烷基、C4-C7烷基環烷基、C4-C7環烷基烷基、C2-C7烷基羰基或C2-C7烷氧基羰基；各R10獨立地為H；或C1-C6烷基、C1-C6鹵代烷基、C2-C6烯基、C2-C6炔基、C3-C6環烷基、C4-C7烷基環烷基或C4-C7環烷基烷基；各R11獨立地為H；或C2-C6烯基、C2-C6炔基、C3-C6環烷基、C4-C7烷基環烷基、C4-C7環烷基烷基、C2-C7烷基羰基、C2-C7烷氧基羰基、C1-C6烷基磺醯基或C1-C6鹵代烷基磺醯基；且各W獨立地為O或S。 The method of claim 1, wherein: Z is optionally substituted with up to 5 substituents independently selected from R2; Q is phenyl or 1-naphthyl, each of which is optionally independently selected from 4 independently selected from 4 Substituted by a substituent of R3; each R2 is independently halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 Haloalkylthio, C1-C6 alkylamino, C2-C6 dialkylamino, -CN or -NO2; each R3 is independently halogen, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 olefin , C2-C6 haloalkenyl, C2-C6 alkynyl, C3-C6 haloalkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C1-C6 alkoxy, C1-C6 Haloalkoxy, C1-C6 alkylthio, C2-C7 alkylcarbonyl, C2-C7 haloalkylcarbonyl, C1-C6 haloalkylthio, C1-C6 alkylsulfinylene, C1-C6 haloalkylsulfinium , C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, -N(R4)R5, -C(=W)N(R4)R5, -C(=W)OR5, -CN, -OR11 or -NO2; or a benzene ring or a 5- or 6-membered saturated or unsaturated heterocyclic ring, each optionally substituted with one or more substituents independently selected from the group consisting of halogen, C1-C6 alkyl , C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio , C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, -CN, -NO2, -N(R4) R5, -C(=W)N(R4)R5, -C(=O)OR5 and R7; each R4 Independently H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C4-C7 alkylcycloalkyl, C4-C7 cycloalkylalkyl, C2- C7 alkylcarbonyl or C2-C7 alkoxycarbonyl; each R5 is independently H; or C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C4-C7 alkane a cycloalkyl group or a C4-C7 cycloalkylalkyl group, each optionally substituted with one or more substituents independently selected from R6; Each R6 is independently halogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinylene, C1-C6 alkylsulfonyl, C1-C6 alkane Amino group, C2-C8 dialkylamino group, C3-C6 cycloalkylamino group, C2-C7 alkylcarbonyl group, C2-C7 alkoxycarbonyl group, C2-C7 alkylaminocarbonyl group, C3-C9 two Alkylaminocarbonyl, C2-C7 haloalkylcarbonyl, C2-C7 haloalkoxycarbonyl, C2-C7 haloalkylaminocarbonyl, C3-C9 halodialkylaminocarbonyl, -OH, -NH2, -CN Or -NO2; or Q1; each R7 is independently a phenyl ring or a pyridyl ring, each ring being optionally substituted with one or more substituents independently selected from R8; each R8 is independently halo, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkyl Sulfonyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C1-C6 alkylamino, C2-C6 dialkylamino, C2-C4 alkylcarbonyl, C2-C4 alkane Oxycarbonyl, C2-C7 alkylaminocarbonyl, C3-C7 dialkylaminocarbonyl, -OH, -NH2, -C(=O)OH, -CN or -NO2; each Q1 is independently a benzene ring or a 5- or 6-membered saturated or unsaturated heterocyclic ring, each optionally substituted with one or more substituents independently selected from the group consisting of halogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkyl Sulfonyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C1-C6 alkylamino, C2-C6 Alkylamino group, -CN, -NO2, -C(=W)N(R9)R10 and -C(=O)OR10; each R9 is independently H, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C4-C7 alkylcycloalkyl, C4-C7 cycloalkylalkyl, C2-C7 alkylcarbonyl or C2-C7 alkoxy Carbonyl; each R10 is independently H; or C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C4-C7 alkylcycloalkyl or C4-C7 cycloalkylalkyl; each R11 is independently H; or C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C4-C7 alkylcycloalkyl, C4-C7 naphthenic An alkyl group, a C2-C7 alkylcarbonyl group, a C2-C7 alkoxycarbonyl group, a C1-C6 alkylsulfonyl group or a C1-C6 haloalkylsulfonyl group; and each W is independently O or S. 如請求項10之方法，其中： Z係；Q係；R2a係鹵素、C1-C2鹵代烷基或C1-C2鹵代烷氧基；R2b係H、鹵素或氰基；R2c係H、鹵素或CF3；R3係C(O)N(R4)R5或C(O)OR5a；R4係H、C2-C7烷基羰基或C2-C7烷氧基羰基；且R5係C1-C6烷基或C1-C6鹵代烷基，各自經一個獨立選自下述之取代基取代：羥基、C1-C6烷氧基、C1-C6烷硫 基、C1-C6烷基亞磺醯基、C1-C6烷基磺醯基、C2-C7烷基胺基羰基、C3-C9二烷基胺基羰基、C2-C7鹵代烷基胺基羰基及C3-C9鹵代二烷基胺基羰基；且R5a係C1-C6烷基、C2-C6烯基或C2-C6炔基，各自視情況經一個或多個獨立選自下述之取代基取代：鹵素、C1-C2烷氧基及視情況經至多5個選自鹵素及C1-C3烷基之取代基取代之苯基。 The method of claim 10, wherein: Z series; Q series; R2a is halogen, C1-C2 haloalkyl or C1-C2 haloalkoxy; R2b is H, halogen or cyano; R2c is H, halogen or CF3; R3 is C(O)N(R4) R5 or C(O)OR5a; R4 is H, C2-C7 alkylcarbonyl or C2-C7 alkoxycarbonyl; and R5 is C1-C6 alkyl or C1-C6 haloalkyl, each independently selected from the group consisting of Substituent substitution: hydroxyl, C1-C6 alkoxy, C1-C6 alkane , C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C2-C7 alkylaminocarbonyl, C3-C9 dialkylaminocarbonyl, C2-C7 haloalkylaminocarbonyl, and C3 a -C9 halodialkylaminocarbonyl; and R5a is a C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl group, each optionally substituted with one or more substituents independently selected from the group consisting of: Halogen, C1-C2 alkoxy and optionally phenyl substituted by up to 5 substituents selected from halogen and C1-C3 alkyl. 如請求項1之方法，其中：Z係視情況經至多5個獨立選自R2之取代基取代之苯基；且各R2獨立為F、Cl、Br、C1-C6烷基、C1-C6氟代烷基、C1-C6烷氧基、C1-C6氟代烷氧基、C1-C6烷硫基或C1-C6氟代烷硫基；該方法進一步包括藉由下述製備式2化合物：(1)形成包含自式5化合物獲得之格氏試劑的反應混合物Z-X 5其中X係I，該格氏試劑係藉由使式5化合物與(a)鎂金屬，或(b)烷基鹵化鎂於醚類溶劑存在時接觸獲得；及隨後(2)使該反應混合物與式6化合物接觸 其中Y係OR11或NR12R13；R11係C1-C5烷基；且R12及R13獨立地為C1-C2烷基；或R12及R13一起作為-CH2CH2OCH2CH2-。 The method of claim 1, wherein: Z is optionally substituted with up to 5 substituents independently selected from R2; and each R2 is independently F, Cl, Br, C1-C6 alkyl, C1-C6 fluorine An alkyl group, a C1-C6 alkoxy group, a C1-C6 fluoroalkoxy group, a C1-C6 alkylthio group or a C1-C6 fluoroalkylthio group; the method further comprising preparing a compound of formula 2 by: 1) forming a reaction mixture ZX 5 comprising a Grignard reagent obtained from a compound of formula 5 wherein X is a compound by reacting a compound of formula 5 with (a) a magnesium metal or (b) an alkyl magnesium halide. Contacting in the presence of an ether solvent; and subsequently (2) contacting the reaction mixture with a compound of formula 6 Wherein Y is OR11 or NR12R13; R11 is C1-C5 alkyl; and R12 and R13 are independently C1-C2 alkyl; or R12 and R13 are taken together as -CH2CH2OCH2CH2-. 如請求項12之方法，其中Z係 R2a係F、Cl、Br、C1-C2氟代烷基或C1-C2氟代烷氧基；R2b係H、F、Cl或Br；且R2c係H、F、Cl、Br或CF3。 The method of claim 12, wherein the Z system R2a is F, Cl, Br, C1-C2 fluoroalkyl or C1-C2 fluoroalkoxy; R2b is H, F, Cl or Br; and R2c is H, F, Cl, Br or CF3. 如請求項1之方法，其中：Z係視情況經至多5個獨立選自R2之取代基取代之苯基；且各R2獨立為F、C1-C6烷基、C1-C6氟代烷基、C1-C6烷氧基、C1-C6氟代烷氧基、C1-C6烷硫基或C1-C6氟代烷硫基；該方法進一步包括藉由下述製備式2化合物：(1)形成包含自式5化合物獲得之格氏試劑的反應混合物 Z-X 5其中X係Cl或Br，該格氏試劑係藉由使式5化合物與(a)鎂金屬，或(b)烷基鹵化鎂於醚類溶劑存在時接觸獲得；及隨後(2)使該反應混合物與式6化合物接觸 其中Y係OR11或NR12R13；R11係C1-C5烷基；且R12及R13獨立地為C1-C2烷基；或R12及R13一起作為-CH2CH2OCH2CH2-。 The method of claim 1, wherein: Z is optionally substituted with up to 5 substituents independently selected from R2; and each R2 is independently F, C1-C6 alkyl, C1-C6 fluoroalkyl, a C1-C6 alkoxy group, a C1-C6 fluoroalkoxy group, a C1-C6 alkylthio group or a C1-C6 fluoroalkylthio group; the method further comprising preparing a compound of the formula 2 by: (1) forming an inclusion Reaction mixture of Grignard reagent obtained from compound of formula 5 ZX 5 wherein X is Cl or Br, and the Grignard reagent is obtained by contacting a compound of the formula 5 with (a) a magnesium metal or (b) an alkyl magnesium halide in the presence of an ether solvent; and subsequently (2) The reaction mixture is contacted with a compound of formula 6 Wherein Y is OR11 or NR12R13; R11 is C1-C5 alkyl; and R12 and R13 are independently C1-C2 alkyl; or R12 and R13 are taken together as -CH2CH2OCH2CH2-. 如請求項14之方法，其中Z係 R2a係F、C1-C2氟代烷基或C1-C2氟代烷氧基；R2b係H或F；且R2c係H、F、或CF3。 The method of claim 14, wherein the Z system R2a is F, C1-C2 fluoroalkyl or C1-C2 fluoroalkoxy; R2b is H or F; and R2c is H, F, or CF3.
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